Sunny's Silver Linings

Clients are already asking their MSPs about AI. Josh Coke of Enforcer joins Sunny Kaila to explain why AI governance is becoming a clear revenue opportunity in the channel, and why identity, data and configuration have to come before the tools. In this conversation: ➥ Why adding more products misses what customers actually need ➥ Why end clients are coming to MSPs asking about AI ➥ What happens when Copilot is turned on without guardrails ➥ How Microsoft Purview can be set up in an afternoon using tools already inside Microsoft 365 Business Premium ➥ Why a 90-day AI activation plan starts with the outcome, not the technology ➥ Three questions that justify any investment: revenue, cost and risk Chapters: 0:00 Welcome and introduction 0:27 Josh's 20-year MSP journey, from Kaseya to Enforcer 2:36 The biggest lesson: solve the customer's problem, not the vendor's 4:09 Security vs. usability, and the tools you already pay for 6:43 How AI changes the problem for MSPs 7:32 Clients are now asking MSPs for AI 9:48 How Enforcer uses AI agents on customer calls 11:13 AI governance as a revenue motion 13:50 The unglamorous foundations leaders skip 14:50 Copilot, data sprawl and a real exposure story 17:13 Purview without the project 17:39 Building a 90-day AI activation plan 18:36 Start with use cases, then governance 20:21 Sunny's quality, speed and time scorecard 22:23 Revenue, cost or risk: the three-question test 23:23 Where to find Josh and the AI Mastermind invite

Attackers are walking through the front door with legitimate credentials, and most MSP security stacks still treat identity as a hygiene checkbox. In this episode of Sunny's Silver Linings, Sunny Kaila sits down with Wilfredo Santiago of Blackpoint Cyber. Wilfredo shares his path from the US Navy to the NSA to the MSP space, then breaks down why identity is now the primary attack surface, why MFA is only the beginning, what separates true managed detection and response from reporting, and how MSPs should approach AI governance. Timestamps 00:00 Welcome 01:45 From hacking video games to the US Navy 04:07 The NSA development program and choosing defense 06:27 The unfair fight and a mission-driven career 08:25 Why every SMB is a target 11:38 Invisible borders and protecting the SMB economy 13:36 Attackers logging in, not breaking in 16:37 Least privilege, just-in-time access, and the Intune example 19:06 Blackpoint's Identity AI agent and machine-speed response 21:50 Why MFA isn't enough, and resilient engineering 24:18 True MDR: the R stands for response 29:03 AI governance, shadow AI, and agents as identities 33:00 Proving zero data retention and blocking unapproved AI 36:13 Where to find Wilfredo Who this is for: MSP owners, security leads, and SMB decision-makers who want to reduce identity risk, evaluate MDR vendors with sharper questions, and put guardrails around AI before it creates new exposure. What you will learn: Why attackers now rely on legitimate credentials, and what continuous identity monitoring looks like How over-provisioned roles like SharePoint admin quietly expand your blast radius Why MFA is a starting point, and how resilient engineering prevents repeat incidents The 2 a.m. Saturday test for judging whether your MDR actually responds How to build an AI governance strategy around asset inventory, risk registers, and treating agents as identities #SunnysSilverLinings #MSP #Cybersecurity #IdentitySecurity #AIGovernance

In this episode of SSL, IT By Design's Sunny Kaila sits down with Shahin Pirooz, cybersecurity veteran and founder of White Dog Cyber, to unpack what it really takes for an MSP to become agentic. Shahin traces his path from enterprise software developer to CTO at Centerbeam to building a unified security platform for MSPs, and shares why "not invented here" thinking is one of the biggest silent killers of good business decisions. The conversation moves into shadow AI, why most security vendors that claim to "do it all" are worth a second look, and a framework for treating AI agents as digital employees, complete with identity, ownership, job scope, and a kill switch. Timestamps: 00:00 – Why agentic MSP education matters right now 00:23 – The "software company masquerading as a service company" thesis 03:10 – Shahin Pirooz's entrepreneurial journey, from EDS to Centerbeam to White Dog Cyber 04:10 – The biggest professional lesson: staying agile when the ground keeps shifting 06:23 – The number one risk in the MSP space: letting pride override good decisions 08:21 – Breaking the "not invented here" mindset with a build vs. buy lens 10:41 – How AI is reshaping cybersecurity for MSPs and their end customers 13:36 – Inside White Dog Cyber's approach: a unified API and data layer instead of MCP sprawl 18:30 – One piece of advice before choosing any security vendor 20:00 – Shadow AI, agent governance, and treating AI agents like digital employees 21:58 – Where to find Shahin Pirooz and White Dog Cyber Who This Is For: MSP owners, operators, and technology leaders who are evaluating how to move toward agentic operations without creating security or governance blind spots. Also valuable for anyone responsible for vendor selection, cybersecurity strategy, or AI adoption inside an MSP. What You Will Learn: Why "not invented here" thinking quietly limits MSP growth, and how to apply a build vs. buy lens instead The real risk behind MCP sprawl when connecting AI agents to security tools Why a unified data layer matters more than a unified interface How to evaluate a security vendor that claims to solve everything A practical framework for governing AI agents as digital employees, including identity, ownership, access scope, and kill switches What shadow AI is, and why it's the next version of shadow IT

I sat down with Greg Jones, SVP at Kaseya, for this episode, and it stayed with me long after we stopped recording. Greg has spent his career across government, MSP, and vendor roles, and he's watched thousands of MSPs make the same mistake: collecting more knowledge instead of executing on what they already have. We talk about his book, The Best of One Minute Wednesday, the knowledge action gap I fell into myself back in 2003, and what it takes to scale without losing yourself in the process. Timestamps: 00:56 – Welcome and guest introduction 01:15 – Greg's journey into the MSP and vendor world 06:21 – The origin story behind One Minute Wednesday 11:09 – Why every leader should write down what they've learned 13:01 – Execution over consumption in the AI era 15:06 – Choosing the right idea and building a 30 day action plan 18:39 – Closing the knowledge action gap 21:05 – Building the capabilities SMBs actually need 22:28 – Becoming a go to market business, not just a tech business 27:03 – Scaling without owner burnout 30:10 – Why peer groups matter, and letting go of the grenade 34:48 – The charity behind the book 36:21 – Where to find The Best of One Minute Wednesday Who this is for: Any MSP owner who has walked out of a conference inspired and walked back into the same routine a week later. Leaders who know they need to delegate more but haven't figured out how. What you will learn: Why knowledge without action is just a hobby How to reverse engineer a plan into weekly execution steps The mindset shift from tech-led to go to market-led How letting go of control is what actually lets a business grow

Sunny Kaila sits down with David Powell of Liongard, a channel veteran and two-time CRN Channel Chief, to unpack why MSPs keep buying tools instead of outcomes. David breaks down the visibility gap most MSPs don't know they have, why AI automation is only as good as the data behind it, and how Liongard's new MCP integration with Claude is changing how MSPs interact with their own asset data. The conversation covers everything from shadow IT to outcome-based billing to what a 90-day AI action plan actually looks like for an MSP owner. Timestamps 00:00 Welcome and Liongard partnership 01:23 David Powell's background and industry recognition 01:53 Tools vs. outcomes: what the industry keeps selling MSPs wrong 02:09 The quarter-inch drill bit story 04:47 Why MSPs need actionable ideas, not more good ideas 05:11 The box of Legos problem 07:36 The MSP visibility gap explained 07:54 Windows and doors: the apartment building analogy 10:45 Shadow IT, shadow AI, and what RMMs miss 11:29 Why RMMs are ephemeral and Liongard keeps 18 months of history 12:57 Why AI only works when the underlying data is right 14:09 The chocolate chip cookie robot: why source of truth matters 17:16 Aunt Evelyn's caramel cake and the MSP documentation problem 19:36 Dirty data and how AI amplifies it 20:55 Liongard's new MCP capability explained 21:15 Demoing Liongard through Claude instead of logging in 22:35 Is Claude becoming the real single pane of glass? 24:11 Data accuracy and the 10x effect on decisions 24:41 Provability and cybersecurity insurance 26:03 Breach liability and the historical record 26:59 The managed intelligence provider maturity model 27:06 Scaling without linear headcount 28:53 The barbell effect: private equity and MSP market polarization 29:18 The shift to outcome-based pricing 31:05 The physician analogy: procedure-based vs. visit-based pay 32:32 A history of MSP billing models, from break-fix to outcomes 34:46 The PC imaging example and efficiency at scale 35:21 David's 90-day action plan for AI-native MSPs 36:24 Why every MSP needs a dedicated AI automation day Who this is for: MSP owners, operators, and technical leaders who are trying to move past tool sprawl and build a real AI automation strategy. Also relevant for anyone evaluating asset intelligence platforms, RMM/PSA data gaps, or outcome-based pricing models. What you will learn: Why MSPs get sold tools instead of outcomes, and how to spot the difference What the "visibility gap" is and why most MSPs don't know what's actually in their environment Why AI automation fails without a reliable source of truth How Liongard's MCP integration with Claude changes how MSPs access their own data Why outcome-based billing is replacing time-based and device-based models A practical, low-cost way to start building an AI automation practice in 90 days #MSP #ManagedServiceProviders #AIforMSPs #AssetIntelligence #ITChannel #MSPGrowth #AIAutomation #ClaudeAI #ITByDesign #Liongard

On this episode of Sunny's Silver Linings, Sunny Kaila sits down with Daniel Gallancy, CEO of Atakama, to examine the browser security gap that most MSPs have yet to address and why shadow AI has made that gap significantly more dangerous. Daniel's career trajectory ran through engineering, finance, and the cryptocurrency world before arriving in cybersecurity. Atakama itself began as encryption software and executed a full pivot to browser security purpose-built for the MSP channel. That pivot and how Daniel led his team through it with clarity and conviction is one of the most instructive leadership threads in this conversation. The episode covers shadow AI as a present operational reality inside SMB environments, not a theoretical future risk. It also explores how browser-level visibility reshapes the MSP sales conversation and what it looks like to lead through product transformation without losing team alignment. 00:00 Introduction and guest welcome 01:14 Daniel's entrepreneurial journey from engineering to cybersecurity 02:50 The origin of the Atakama name 04:55 The blind spot in traditional endpoint security stacks 07:08 How AI has changed the security threat landscape for MSPs and their clients 10:33 Shadow AI: what MSP leaders are encountering every week 12:36 How Atakama addresses shadow AI at the browser level 16:56 How browser security helps MSPs grow, sell, and retain clients 20:25 The opening question MSPs can use to start a browser security conversation 23:41 Leadership lesson: communicating through a major product pivot 29:10 Looking ahead: where the MSP security stack is heading 30:05 Life lesson from Daniel: the discipline of responding rather than reacting Who This Is For: MSP owners and CEOs evaluating browser security as a new practice area, technology leaders assessing shadow AI visibility and data governance controls, and MSP operators who want a firsthand account of how a cybersecurity company navigated a full product pivot while maintaining team alignment and market momentum. What You Will Learn: Why the browser is the current blind spot in most MSP security stacks and why endpoint tools alone are not enough What shadow AI is, why its non-malicious nature makes it harder to govern, and why that distinction matters for MSP conversations How Atakama surfaces shadow AI activity and client data uploads to MSPs in real time What browser visibility data looks like in a client-facing or prospect-facing conversation The single question MSPs can ask an SMB decision-maker to open a browser security discussion How Daniel maintained team focus and operational momentum through a complete product pivot What the distinction between responding and reacting means at both the leadership and personal level #MSP #CyberSecurity #ShadowAI #BrowserSecurity #AIGovernance #ManagedServices #MSPGrowth #SunnySilverLinings #ITByDesign #ManagedIntelligence

Serge Bukhar spent ten years inside an MSP, watched it grow from 80 to 400 people, then built something of his own. Ten years later, Atlas Technica is a 400-person pure-play MSP serving the alternative investment industry exclusively. In this episode, Sunny Kaila sits down with Serge to unpack what drove that growth, how Atlas Technica is approaching AI adoption internally and for clients, and why creating space for your team to talk may be the most important leadership move right now. TIMESTAMPS 00:37 From Engineer to Entrepreneur: The Atlas Technica Story 01:22 The Mistake Most MSPs Make: Prioritizing Sales Over Service 02:44 Happy Employees Create Happy Clients 04:48 Building a Pure-Play MSP for Alternative Investment Firms 05:21 Why Measured Growth Beats Growth at Any Cost 05:55 Using AI to Improve Efficiency, Delivery & Client Outcomes 07:18 Why Governance, Compliance & Security Must Come Before AI 09:20 Helping Clients Separate AI Hype from Business Value 10:25 The Dot-Com Comparison: What Today's AI Market Can Learn 12:00 Why MSPs Should Avoid Betting on a Single AI Vendor 15:00 Securing Employee Buy-In for AI Adoption 16:24 How Atlas Technica Implemented Glean Across the Organization 17:32 Driving Adoption Through Communication & Internal Hackathons 19:21 The Reality Check: AI Won't Take Your Job, Someone Using It Better Might 20:24 How Client Demand for AI Changed Almost Overnight 21:27 Why Businesses of Every Size Can Benefit from AI Today 23:50 Turning AI Capabilities Into Growth & Upsell Opportunities 25:36 Serge's Top Leadership Advice: Listen to Your Employees 26:16 Creating Safe Spaces for AI Conversations & Innovation Who this is for: MSP owners and operators looking to scale with intention, leaders navigating internal AI adoption, and anyone working to turn AI into a real business practice. What you will learn: Why service delivery is the real growth driver for MSPs, not sales or technology How Atlas Technica used Glean to give 400 employees practical access to AI How to help clients navigate AI vendor selection without chasing hype Why hedging across multiple AI vendors matters more than committing to one How to identify and retain AI-forward thinkers already inside your organization #AIbyDesign #MSP #ManagedServices #AIAdoption #MSPGrowth #ArtificialIntelligence #ITByDesign #SunnyKaila #AtlasTechnica #AlternativeInvestments #ServiceDelivery #TechLeadership

The MSPs who resisted the cloud in 2013 didn't disappear overnight, but they became last year's business fast. The same shift is happening right now with AI, and it's moving at a speed that won't give anyone a decade to catch up. In this episode, Sunny sits down with various MSP leaders to unpack what it takes to lead a business through this moment, financially, mentally, and operationally. Timestamps: 00:00 — Why embracing AI is non-negotiable for MSPs right now 01:29 — Running a weekly AI Accelerator for MSP leaders 02:08 — "AI won't replace MSPs. AI-powered MSPs will replace MSPs" 03:20 — Why culture and cash are not in conflict 04:27 — Teaching your team the financials: the leadership move most skip 07:56 — DSO explained: the number that changes MSP cash flow overnight 07:59 — Readiness is not a state of being. It's what happens after you act 10:43 — The backwards confidence model: action first, confidence second 11:34 — Being stuck is not a problem. It's a signal Who this is for: MSP owners and operators who want to lead through the AI transition, improve financial health, and stop waiting for the "right moment" to make their next move. What you will learn: Why the AI transition will move faster than the cloud shift and what that means for MSPs who hesitate The difference between AI replacing MSPs vs. AI-powered MSPs outcompeting everyone else How to use DSO as a practical lever to improve cash flow and business health Why financial transparency with your team builds culture, not undermines it The backwards confidence model: why action creates readiness, not the other way around How to reframe being "stuck" as a signal for growth, not a failure state

Most MSP leaders are busy. But busy is not the same as building. In this video, Sunny Kaila breaks down different conversations that reveal the habits, mindsets, and practices that separate leaders who scale from those who stall. Who this is for: MSP owners, founders, and leaders who want to build something that lasts, not just manage what they already have. What you will learn: Why planning more than you think you need to is the foundation most MSPs skip How the shiny toy syndrome quietly kills momentum in growing businesses Why bad decisions are always better than indecision, and how to build that muscle The difference between perception and perspective, and why it changes how you lead, hire, and close A reverse culture fit interview technique that builds buy-in before day one #MSP #ManagedServices #MSPLeadership #SunnyKaila #AIbyDesign #BusinessGrowth #LeadershipDevelopment #DecisionMaking #CompanyCulture #MSPBusiness